Water → (3-chloro-5-trifluoromethyl-2-pyridyloxymethyl)-alpha-methoxy-N-methyl-phenylacetamide

HRID 427994Notes

Reaction equation

HRID 427994 reaction equation
OC[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([O:14][CH3:15])[C:10]([NH:12][CH3:13])=[O:11].[H-].[Na+].Cl[C:19]1[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][N:20]=1.O.CN(C)[CH:33]=[O:34]>>[Cl:25][C:24]1[C:19]([O:34][CH2:33][C:9]([C:4]2[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=2)([O:14][CH3:15])[C:10]([NH:12][CH3:13])=[O:11])=[N:20][CH:21]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:23]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 702393162-hydroxymethyl-alpha-methoxy-N-methyl-phenylacetamide

Product 1

HCID 18357813(3-chloro-5-trifluoromethyl-2-pyridyloxymethyl)-alpha-methoxy-N-methyl-phenylacetamideYield 75%

Conditions

Temperature
0 °C

Procedure

A solution of 2-hydroxymethyl-α-methoxy-N-methyl-phenylacetamide (1.00 g, 4.8 mmol) in N,N-dimethylformamide (5 ml) was stirred at 0° C., and 60% oily sodium hydride (0.19 g, 4.8 mmol) was added thereto. The mixture was stirred at 0° C. for 30 minutes, and then 2,3-dichloro-5-trifluoromethylpyridine (1.24 g, 5.7 mmol) was added. The mixture was stirred at 0° C. for 2 hours, and then ice and water were added in this order. The mixture was extracted with ether, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1) to give the desired compound (3-chloro-5-trifluoromethyl-2-pyridyloxymethyl)-α-methoxy-N-methyl-phenylacetamide (1.40 g, 75%) as

Workup

  1. stirringThe mixture was stirred at 0° C. for 2 hours
  2. extractionThe mixture was extracted with ether
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-77a06f1c09be4650a7131542a7e4b97c
Source dataset
uspto-grants-2001_11
Patent number
US06313150B1

Reaction notes

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